The show featured The Brothers Chaps and Missy Palmer performing live music while being backed by Yacht Rock Revue. Some of the music performances included video content, and puppets were featured as well. Some people dressed up as characters from the Homestar Runner body of work.

At some point during the performances, the video AV stopped working, so Matt Chapman started singing bread sing-alongs with Puppet Homestar Runner, who said that the songs had the power to fix AV problems. This eventually became a running gag. After an intermission, Limozeen played, and flicked Limozeen guitar picks into the audience. The picks were previously shown in a @StrongBadActual Tweet. Towards the end, Matt invited Jamey Huggins, the person who thought of the name "Homestar Runner", to the stage to tell that story. Before performing the final song, Secret Song, Matt said that normally they'd have to wait 227 seconds before hearing it, like on Strong Bad Sings and Other Type Hits. At the end of the show, Matt said "Here's to twenty more years of making stupid stuff!", which was responded with a loud cheer from the audience.

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